ZA200600769B - Sulfonamide substituted imidazoquinolines - Google Patents
Sulfonamide substituted imidazoquinolines Download PDFInfo
- Publication number
- ZA200600769B ZA200600769B ZA200600769A ZA200600769A ZA200600769B ZA 200600769 B ZA200600769 B ZA 200600769B ZA 200600769 A ZA200600769 A ZA 200600769A ZA 200600769 A ZA200600769 A ZA 200600769A ZA 200600769 B ZA200600769 B ZA 200600769B
- Authority
- ZA
- South Africa
- Prior art keywords
- imidazo
- quinolin
- compound
- formula
- amino
- Prior art date
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- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 8
- 229940124530 sulfonamide Drugs 0.000 title description 7
- 125000000565 sulfonamide group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 83
- 150000003839 salts Chemical class 0.000 claims description 25
- 108090000695 Cytokines Proteins 0.000 claims description 24
- 102000004127 Cytokines Human genes 0.000 claims description 24
- 241001465754 Metazoa Species 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000001939 inductive effect Effects 0.000 claims description 9
- 230000003612 virological effect Effects 0.000 claims description 9
- 230000001613 neoplastic effect Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 229910052739 hydrogen Inorganic materials 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 239000007787 solid Substances 0.000 description 26
- 229910052799 carbon Inorganic materials 0.000 description 25
- 238000007429 general method Methods 0.000 description 21
- 125000000217 alkyl group Chemical group 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 17
- 125000000623 heterocyclic group Chemical group 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 238000007796 conventional method Methods 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- -1 1,1-dioxidoisothiazolidin-2-yl Chemical group 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 7
- 150000001204 N-oxides Chemical class 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 230000028993 immune response Effects 0.000 description 7
- GCGNWZMOENODOJ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinoline Chemical class C1C=C2C=CC=NC2=C2C1NCN2 GCGNWZMOENODOJ-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000004103 aminoalkyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- 150000003456 sulfonamides Chemical group 0.000 description 6
- HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical group C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 4
- YHQPYMQQMBVULM-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinolin-4-amine Chemical class C1CCCC2=C1N=C(N)C1=C2NC=N1 YHQPYMQQMBVULM-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 230000009385 viral infection Effects 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XYYKPSXKBVBMHJ-UHFFFAOYSA-N 3-(2-butylimidazo[4,5-c]quinolin-1-yl)propan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCN)C3=CN=C21 XYYKPSXKBVBMHJ-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 229940124669 imidazoquinoline Drugs 0.000 description 3
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- KCQWOAPKZGATTP-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 KCQWOAPKZGATTP-UHFFFAOYSA-N 0.000 description 3
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- SKPRPEJLFKCOAB-UHFFFAOYSA-N 3-nitroquinolin-4-amine Chemical compound C1=CC=C2C(N)=C([N+]([O-])=O)C=NC2=C1 SKPRPEJLFKCOAB-UHFFFAOYSA-N 0.000 description 2
- LTPVCZQGBDHLMG-UHFFFAOYSA-N 4-(2-ethylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCN)C3=CN=C21 LTPVCZQGBDHLMG-UHFFFAOYSA-N 0.000 description 2
- BHBQPNUVSWIHOD-UHFFFAOYSA-N 4-(2-hexylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=N3)CCCCN)C3=CN=C21 BHBQPNUVSWIHOD-UHFFFAOYSA-N 0.000 description 2
- HKHKLZGFYFCZFA-UHFFFAOYSA-N 4-(2-propylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCN)C3=CN=C21 HKHKLZGFYFCZFA-UHFFFAOYSA-N 0.000 description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| US48320003P | 2003-06-27 | 2003-06-27 |
Publications (1)
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| ZA200600769B true ZA200600769B (en) | 2007-05-30 |
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| JP (1) | JP2007521280A (es) |
| KR (1) | KR20060035637A (es) |
| CN (1) | CN1812789B (es) |
| AR (2) | AR044922A1 (es) |
| AU (1) | AU2004253929A1 (es) |
| BR (1) | BRPI0411916A (es) |
| CA (1) | CA2529322A1 (es) |
| IL (1) | IL172427A0 (es) |
| MX (1) | MXPA06000144A (es) |
| MY (1) | MY157827A (es) |
| NZ (1) | NZ544330A (es) |
| RU (1) | RU2374246C2 (es) |
| TW (2) | TW200511992A (es) |
| WO (2) | WO2005003064A2 (es) |
| ZA (1) | ZA200600769B (es) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| JP2007502293A (ja) | 2003-08-12 | 2007-02-08 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドロキシルアミン置換イミダゾ含有化合物 |
| EP1658076B1 (en) | 2003-08-27 | 2013-03-06 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| CA2537763A1 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for cd5+ b cell lymphoma |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| WO2005079195A2 (en) | 2003-10-03 | 2005-09-01 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| AR046046A1 (es) | 2003-10-03 | 2005-11-23 | 3M Innovative Properties Co | Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas. |
| CA2545825A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| CA2545774A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| BRPI0416936A (pt) | 2003-11-25 | 2007-01-16 | 3M Innovative Properties Co | sistemas de anel de imidazo substituìdos e métodos |
| EP1689361A4 (en) * | 2003-12-02 | 2009-06-17 | 3M Innovative Properties Co | THERAPEUTIC COMBINATIONS AND PROCESSES WITH IRM COMPOUNDS |
| EP1701955A1 (en) | 2003-12-29 | 2006-09-20 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| EP1699788A2 (en) | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides |
| AU2005228150A1 (en) | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005123080A2 (en) | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| WO2006009826A1 (en) | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| WO2006038923A2 (en) | 2004-06-18 | 2006-04-13 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| JP5543068B2 (ja) | 2004-12-30 | 2014-07-09 | スリーエム イノベイティブ プロパティズ カンパニー | キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| JP2008526757A (ja) * | 2004-12-30 | 2008-07-24 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節剤製剤および方法 |
| US8034938B2 (en) | 2004-12-30 | 2011-10-11 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| US9248127B2 (en) | 2005-02-04 | 2016-02-02 | 3M Innovative Properties Company | Aqueous gel formulations containing immune response modifiers |
| US20080318998A1 (en) | 2005-02-09 | 2008-12-25 | Coley Pharmaceutical Group, Inc. | Alkyloxy Substituted Thiazoloquinolines and Thiazolonaphthyridines |
| EP1846405A2 (en) | 2005-02-11 | 2007-10-24 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted imidazo 4,5-c ring compounds and methods |
| US7943610B2 (en) | 2005-04-01 | 2011-05-17 | 3M Innovative Properties Company | Pyrazolopyridine-1,4-diamines and analogs thereof |
| CA2602590A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| AU2006287270A1 (en) * | 2005-09-09 | 2007-03-15 | Coley Pharmaceutical Group, Inc. | Amide and carbamate derivatives of N-{2-[4-amino-2- (ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods |
| ZA200803029B (en) * | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| AU2006292119A1 (en) * | 2005-09-23 | 2007-03-29 | 3M Innovative Properties Company | Method for 1H-imidazo[4,5-c]pyridines and analogs thereof |
| WO2007100634A2 (en) | 2006-02-22 | 2007-09-07 | 3M Innovative Properties Company | Immune response modifier conjugates |
| WO2008008432A2 (en) | 2006-07-12 | 2008-01-17 | Coley Pharmaceutical Group, Inc. | Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods |
| PL2276486T3 (pl) * | 2008-03-24 | 2014-04-30 | 4Sc Discovery Gmbh | Nowe podstawione imidazochinoliny |
| ES2943385T3 (es) | 2010-08-17 | 2023-06-12 | 3M Innovative Properties Company | Compuesto modificador de la respuesta inmunitaria lipidada y su uso médico |
| MX355623B (es) | 2011-06-03 | 2018-04-25 | 3M Innovative Properties Co | Hidrazino-1h-imidazoquinolin-4-aminas y conjugados elaborados a partir de las mismas. |
| US9475804B2 (en) | 2011-06-03 | 2016-10-25 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| EP3083618B1 (en) | 2013-12-17 | 2018-02-21 | Pfizer Inc | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| JP6873980B2 (ja) * | 2015-09-14 | 2021-05-19 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規のイミダゾ［４，５−ｃ］キノリンおよびイミダゾ［４，５−ｃ］［１，５］ナフチリジン誘導体 |
| KR20230149857A (ko) | 2016-07-07 | 2023-10-27 | 더 보드 어브 트러스티스 어브 더 리랜드 스탠포드 주니어 유니버시티 | 항체-애쥬번트 접합체 |
| CA3056030A1 (en) | 2017-03-10 | 2018-09-13 | Pfizer Inc. | Novel imidazo[4,5-c]quinoline derivatives as lrrk2 inhibitors |
| SG11202001926QA (en) | 2017-09-06 | 2020-04-29 | BioNTech SE | Substituted imidazoquinolines as agonists of tlr7 |
| EP3728255B1 (en) | 2017-12-20 | 2022-01-26 | 3M Innovative Properties Company | Amide substituted imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
| WO2020190725A1 (en) | 2019-03-15 | 2020-09-24 | Bolt Biotherapeutics, Inc. | Immunoconjugates targeting her2 |
| AU2020407871A1 (en) * | 2019-12-20 | 2022-06-30 | Nammi Therapeutics, Inc. | Formulated and/or co-formulated liposome compositions containing toll-like receptor ("TLR") agonist prodrugs useful in the treatment of cancer and methods thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| JP2005513021A (ja) * | 2001-11-16 | 2005-05-12 | スリーエム イノベイティブ プロパティズ カンパニー | Ｉｒｍ化合物およびトール様受容体経路に関する方法および組成物 |
| US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
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2004
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- 2004-06-25 WO PCT/US2004/020606 patent/WO2005003064A2/en not_active Application Discontinuation
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- 2004-06-25 AR ARP040102247A patent/AR044922A1/es unknown
- 2004-06-25 AR ARP040102248A patent/AR044923A1/es unknown
- 2004-06-25 EP EP04756208A patent/EP1638566A4/en not_active Withdrawn
- 2004-06-25 KR KR1020057024904A patent/KR20060035637A/ko not_active Application Discontinuation
- 2004-06-25 TW TW093118636A patent/TW200511992A/zh unknown
- 2004-06-25 NZ NZ544330A patent/NZ544330A/en unknown
- 2004-06-25 AU AU2004253929A patent/AU2004253929A1/en not_active Abandoned
- 2004-06-25 RU RU2005138915/04A patent/RU2374246C2/ru not_active IP Right Cessation
- 2004-06-25 MX MXPA06000144A patent/MXPA06000144A/es unknown
- 2004-06-25 CA CA002529322A patent/CA2529322A1/en not_active Abandoned
- 2004-06-25 CN CN2004800181459A patent/CN1812789B/zh not_active Expired - Fee Related
- 2004-06-25 WO PCT/US2004/020607 patent/WO2005003065A2/en active Application Filing
- 2004-06-25 TW TW093118635A patent/TW200514784A/zh unknown
- 2004-06-25 BR BRPI0411916-9A patent/BRPI0411916A/pt not_active IP Right Cessation
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2005
- 2005-12-07 IL IL172427A patent/IL172427A0/en unknown
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2006
- 2006-01-26 ZA ZA200600769A patent/ZA200600769B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005003065A2 (en) | 2005-01-13 |
| MY157827A (en) | 2016-07-29 |
| NZ544330A (en) | 2009-06-26 |
| AR044923A1 (es) | 2005-10-12 |
| EP1638566A4 (en) | 2009-03-25 |
| EP1638566A2 (en) | 2006-03-29 |
| WO2005003065A3 (en) | 2005-03-10 |
| AU2004253929A1 (en) | 2005-01-13 |
| TW200514784A (en) | 2005-05-01 |
| RU2374246C2 (ru) | 2009-11-27 |
| IL172427A0 (en) | 2006-04-10 |
| WO2005003064A3 (en) | 2005-03-31 |
| BRPI0411916A (pt) | 2006-08-15 |
| MXPA06000144A (es) | 2006-04-07 |
| CA2529322A1 (en) | 2005-01-13 |
| CN1812789A (zh) | 2006-08-02 |
| TW200511992A (en) | 2005-04-01 |
| WO2005003064A2 (en) | 2005-01-13 |
| AR044922A1 (es) | 2005-10-12 |
| RU2005138915A (ru) | 2006-06-27 |
| KR20060035637A (ko) | 2006-04-26 |
| CN1812789B (zh) | 2010-07-14 |
| JP2007521280A (ja) | 2007-08-02 |
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